From Wine Country to the Caribbean

Thanksgiving offers that rare long weekend when travel feels indulgent rather than rushed. Whether you’re craving turkey by the beach, mountain views by the fireplace, or a holiday somewhere completely new, this year’s timing couldn’t be better.

From tropical beach resorts in Mexico and the Caribbean to cozy retreats in California and Vermont, here are the best places to unwind (and feast) over the long weekend, plus a few international ideas if you’re ready to head abroad.

Tropical Beach Escapes: Mexico & the Caribbean

Thanksgiving may be unique to the United States, but that doesn’t mean you have to stay stateside to celebrate, especially when somewhere warm and sunny is calling.

One&Only Mandarina, Riviera Nayarit, Mexico

Carved into rainforest-covered cliffs overlooking a pristine bay, One&Only Mandarina is a rainforest-meets-ocean hideaway of ultra-luxe treehouses and villas, perfect for families or groups. Over the holiday weekend, the resort goes all out: little ones make gratitude cards and enjoy makeovers at the KidsOnly Club, while adults join cacao ceremonies on the Aura Deck or the signature Thanksgiving Polo Brunch (yes, with a live polo match).

The main event is a Thanksgiving feast curated by Chef Enrique Olvera, of Mexico City’s famed Pujol, at his on-site restaurant Carao, an autumn-inspired buffet that reimagines the holiday, Mexican-style.

Next door, along the same secluded stretch of coastline, Rosewood Mandarina (newly opened this year) adds another layer of luxury to this Riviera Nayarit enclave, with access to many of the same amenities.

Perks include: daily breakfast, $100 hotel credit, and priority upgrades with flexible check-in/out whenever available.

Cap Juluca, A Belmond Hotel, Anguilla

Curving along Maundays Bay, Belmond Cap Juluca is the definition of understated Caribbean luxury , whitewashed villas, private terraces, and that luminous turquoise water Anguilla is known for.

Over Thanksgiving, the resort keeps things elegant yet relaxed, starting with brunch at Cip’s by Cipriani and ending with a candlelit dinner at Pimms, where island-inspired dishes and warm hospitality set the tone. Between meals, guests can join yoga classes at the Events Pavilion, try Rockside fishing, or drift between beach and sea. As the sun sets, the hotel’s nightly Champagne sabering ritual is the perfect punctuation to another slow, sun-soaked day.

Nearby, Aurora Anguilla Resort & Golf Club offers a more family-friendly alternative , expansive suites, multiple pools, and a lively, all-ages vibe. With its beachfront location on Rendezvous Bay, golf course, and water park, it’s ideal for those who want Anguilla’s beauty with a more relaxed energy.

Perks include: daily breakfast, $100 hotel credit, a welcome amenity, and upgrades or flexible check-in/out when available.

Food & Wine Getaways: California & Charleston

If your idea of Thanksgiving involves great wine, chef-driven menus, and maybe fewer dishes to wash, these gourmet getaways deliver.

Stanly Ranch, Auberge Resorts Collection, Napa Valley, California

Thanksgiving at Stanly Ranch is a multi-day, multi-generational affair, and if any brand knows how to curate family-friendly luxury, it’s Auberge. This year’s celebration includes everything from pumpkin carving and block-printing workshops to the annual Turkey Trot, pasta-making in The Grange, and a cozy Thanksgiving dinner at Bear, where Chef Anthony Stagnaro pairs California ingredients with classic holiday flavors.

Families can make caramel apples, craft wreaths, or sip mulled wine during the resort’s “Hanging with Hootbert” owl meet-up, while adults sneak off to the Halehouse Spa for a restorative treatment between festivities.

For an under-the-radar alternative, head north to Montage Healdsburg, where rolling vineyards and Michelin-level dining offer another unforgettable way to spend the weekend.

Perks include: daily breakfast, $100 credit, a welcome amenity, and upgrades or flexible check-in/out whenever available.

The Dewberry, Charleston, South Carolina

With its cobblestoned streets, oak-lined squares, and restaurants that take Southern cooking seriously, Charleston makes a perfect Thanksgiving getaway.

The Dewberry, set in a restored mid-century landmark overlooking Marion Square, puts you right in the center of it all. The hotel’s restaurant, Henrietta’s, serves a festive feast that pairs regional favorites with Thanksgiving classics, while the rooftop Citrus Club is perfect for sunset cocktails. Beyond the hotel, the city comes alive with oyster roasts, harbor walks, and just the right hint of fall chill.

Perks include: daily breakfast credit ($45 per person), $100 hotel credit, and upgrades or extended check-in/out whenever possible.

Nature Retreats: Vermont & Montana

If your Thanksgiving dreams lean more toward mountain air and cozy cabins than cities or beach chairs, these retreats deliver space to slow down, reconnect, and savor the season.

Twin Farms, Vermont

At Twin Farms, Thanksgiving feels like stepping into a storybook version of New England in autumn. Tucked into Vermont’s rolling hills, this adults-only retreat is surrounded by forest, meadows, and the kind of golden light that makes late November magical.

Each of the 20 individually designed cottages and suites features museum-worthy art, wood-burning fireplaces, and deep-soaking tubs. Service here is famously intuitive, every stay is personalized down to your favorite wine and snack.

On Thanksgiving Day, guests gather for cocktails and canapés before Chef Nathan Rich and his team serve a multi-course dinner reimagining traditional dishes with local, seasonal ingredients, farm-raised turkey, roasted root vegetables, and Vermont wines. It’s festive, elegant, and quietly spectacular.

Perks include: a Twin Farms Farm-to-Table Gift Set (value $140 USD), daily breakfast, and upgrades or flexible check-in/out when available.

Paws Up, Montana

If Thanksgiving at Twin Farms is fireside elegance, Paws Up is all about big skies and family adventure.

Set on a 37,000-acre working cattle ranch, the resort offers a full weekend of new traditions, horseback rides, hayrides, petting zoos, and cookie-decorating contests. Evenings bring bluegrass music, game nights, and s’mores around the fire. The Thanksgiving feast can be enjoyed at Pomp or delivered privately to your cabin (and cleared away afterward).

This year, Paws Up partners with Rombauer Vineyards for special wine pairings, plus live acoustic music by Dan Dubuque, the perfect mix of Montana charm and holiday warmth.

Just next door, The Green O, Paws Up’s adults-only sister property, offers a quieter, design-forward alternative for couples.

Perks include: $300 activity credit, complimentary airport transfers, a bottle of wine on arrival, daily breakfast, and upgrades or flexible check-in/out when available.

Cozy City Stays: New York & Québec City

If your idea of Thanksgiving involves city lights over mountain peaks, these festive stays deliver holiday atmosphere — no cooking required.

The Whitby Hotel, New York City

Just steps from the Macy’s Thanksgiving Day Parade route, The Whitby Hotel is a colorful, design-forward escape in Midtown Manhattan.

While you can’t see the parade directly from your room, you’re close enough to claim a prime viewing spot before retreating to Kit Kemp’s signature interiors, full of color, pattern, and whimsy. This year’s Thanksgiving menu features elevated classics like heritage black turkey with chestnut stuffing and pumpkin bread pudding with maple-brown butter ice cream, served in The Whitby Bar & Restaurant.

With connecting rooms for families and Central Park, Broadway, Rockefeller Plaza, and the Met just minutes away, it’s the perfect home base for a festive long weekend in the city.

Perks include: $100 food & beverage credit, welcome amenity, daily breakfast, and upgrades or flexible check-in/out when available.

Auberge Saint-Antoine, Québec City

If you’d rather swap parade crowds for cobblestone streets, Auberge Saint-Antoine in Québec City is a perfect Thanksgiving-weekend alternative.

Set within 18th- and 19th-century warehouses in the city’s historic Old Port, this Relais & Châteaux gem is all flickering fireplaces, stone walls, and understated elegance. After exploring Old Québec, a UNESCO World Heritage site that feels like a holiday postcard, return for dinner at Chez Muffy, where Québécois dishes and local wines make staying in feel as rewarding as venturing out.

Perks include: daily breakfast, $100 food & beverage credit, and upgrades or flexible check-in/out when available.

Bonus: Italy Is Always a Good Idea

Because let’s be honest, Thanksgiving in Tuscany may quickly become your new favorite tradition.

Rosewood Castiglion del Bosco, Tuscany, Italy

Set amid the rolling hills of Val d’Orcia, near Montalcino, Rosewood Castiglion del Bosco spans 5,000 acres of vineyards, cypress groves, and golden countryside.

Here, Thanksgiving takes on a Tuscan rhythm: relaxed, elegant, and paired with Brunello. Guests can go truffle-hunting, join a cooking class, or tour the estate’s winery before sitting down to a festive dinner with Castiglion del Bosco wine pairings.

Children can join nature walks and workshops at La Canonica Cooking School, while adults unwind at the spa or explore Montalcino.

Perks include: daily breakfast, €95 food & beverage or spa credit, a welcome amenity, and upgrades when available.

Ready to Plan Your Thanksgiving Escape?

Whether you picture yourself sipping wine in Napa, stargazing in Montana, or feasting under the Caribbean sun, I can help you plan a Thanksgiving weekend that feels easy, inspired, and entirely your own.

Reach out anytime to start designing your holiday getaway, and make this Thanksgiving one to truly remember.

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Where to Go for Thanksgiving 2025